Imidazolidinedione compounds and their uses
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example 1
4-[7-(4-cyano-2-trifluoromethyl-phenyl)-8-oxo-6-thio-5,7-diazaspiro[3,4]-5-octyl]-2-fluoro-N-methyl benzamide (compound 7, as control compound 1)
[0086]
Synthesis of 4-isothiocyanato-2-(trifluoromethyl)-benzyl cyanide (compound 2)
[0087]Into an aqueous suspension (50 mL) of thiophosgene (30.2 g, 262.4 mmol) compound 1 (10.0 g, 53.7 mmol) was slowly added in portions. The reaction mixture was stirred at room temperature (20° C.) for one hour and then extracted with ethyl acetate for three times (3×50 mL). The organic layer was combined, washed with saturated brine (100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a black solid. After purified by column chromatography, a white solid (Compound 2, 11.24 g, yield 92%) was obtained. 1H NMR (CDCl3, 400 MHz): δ(ppm) 7.85 (1H, d, J=8 Hz), 7.59 (1H, s), 7.48 (1H, d, J=8.4 Hz). MS: 229 (M+H+).
Synthesis of 2-fluoro-N-methyl-4-nitro-benzamide (Compound 4)
[0088]
[0089]Into a dichloromethane solution (200 mL) of compou...
example 2
4-[7-(4-cyano-2-trifluoromethyl-phenyl)-8-oxo-6-thio-5,7-diazaspiro[3,4]-5-octyl]-2-fluoro-N,N-dimethyl benzamide (Compound 11)
[0096]
Synthesis of 2-fluoro-N,N-dimethyl-4-nitro-benzamide (Compound 8)
[0097]
[0098]Into a solution of compound 3 (25 g, 135.06 mol) in methylene chloride (200 mL)
[0099]CDI (32.8 g, 202.28 mmol) was added. The reaction mixture was stirred at room temperature for one hour. Into a solution of dimethylamine hydrochloride (13.22 g, 162.12 mmol) in dichloromethane (50 mL) triethylamine (20.47 g, 202.29 mmol) was added to give a white suspension. After stirred at room temperature for half an hour, the suspension was added to the reaction mixture slowly. After the resulting mixture was stirred for one hour, the reaction was quenched by adding water (100 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane twice (2×50 mL). The organic phases were combined, washed with 1 M hydrochloric acid twice (2×50 mL), 1 M aqueous sodium h...
example 3
4-[7-(4-cyano-2-trifluoromethyl-phenyl)-8-oxo-6-thio-5,7-diazaspiro[3,4]-5-octyl]-2-fluoro-N-trideuteromethyl-benzamide (compound 15)
[0106]
Synthesis of 2-fluoro-N-trideuteromethyl-4-nitro-benzamide (compound 12)
[0107]
[0108]Into a solution of compound 3 (5.25 g, 28.37 mol) in dichloromethane (20 mL) CDI (4.62 g, 28.37 mmol) was added. The reaction mixture was stirred at room temperature for one hour. Into a solution of trideuterated methylamine hydrochloride (2 g, 28.76 mmol) in methylene chloride (20 mL) triethylamine (3.27 g, 32.36 mmol) was added to give a white suspension. After stirred at room temperature for half an hour, the suspension was added to the reaction mixture slowly. The resulting mixture was stirred for another hour, the reaction was quenched by adding water (10 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (2×20 mL) twice. The organic phases were combined, washed with 1 M hydrochloric acid (2×10 mL) twice, 1 M aqueous...
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